Total synthesis of (-)-safracin B total synthesis of (-)-thiangazole development of sulfonamide chemistry
Doctor of Philosophy
Chapter I describes the stereocontrolled total synthesis of ($-$)-safracin B with antibacterial and antitumor activities. The convergent approach for the synthesis of safracin B can be readily applied to the synthesis of the related isoquinolinequinone family such as saframycins and ecteinascidins. Chapter II discusses the total synthesis of ($-$)-thiangazole, a substance with potent anti-HIV-1 activity in vitro. An efficient synthetic pathway is developed to enable diverse modification of both ends of thiangazole and thus provide a rapid access to a variety of analogs. Chapter III outlines the development of new chemistry of nitrobenzenesulfonamides, N-Boc and N-Alloc nitrobenzene sulfonamides, and alkylsulfonamides for the efficient preparation of secondary amines and protected primary amines.
Organic chemistry; Pharmaceutical chemistry